


Dirk/Jake MSPARP and Pesterchum logs

by Ine



Category: Homestuck
Genre: Crossdressing Kink, M/M, Masturbation, Online Relationship, Oral Sex, RP-within-RP, Roleplay, msparp.com, pesterchum
Language: English
Status: In-Progress
Published: 2013-05-28
Updated: 2013-05-28
Packaged: 2017-12-13 06:29:42
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 4,158
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/821117
Author URL: https://archiveofourown.org/users/Ine/pseuds/Ine
Summary: <blockquote class="userstuff">
              <p>A collection of worthy RP sessions between Dirk Strider and Jake English. Each chapter will be filled with one session. (Now with canon Pesterchum fonts)</p>
            </blockquote>





	Dirk/Jake MSPARP and Pesterchum logs

Author's notes: This session was played in Pesterchum. I never identified the person who played Jake. I gave them my Pesterchum handles though. If I ever chat with them I'll add their handle here if they want. We talked about continuing this.

As you can imagine, I played Dirk.

* * *

 

\-- timaeusTestified [TT] began pestering golgothasTerror [GT] at 00:01 --

[12:01] TT: Jake? You there?  
[12:03] GT: Oh! Yes. Sorry dirk.  
[12:03] GT: I was getting something to eat.  
[12:03] GT: Whats up?  
[12:04] TT: Oh, there you are.  
[12:04] TT: Uh, not much, just wanted to see how you were doing. <3  
[12:04] GT: Yes! Sorry about the two minute or three or whatever it was wait. Like i said i was spending some time in the kitchen getting something to eat and...  
[12:04] GT: Pffft!  
[12:04] GT: Hearts man?? Youre such a friggin dork!  
[12:05] GT: Ok sure ill toss you back an ironic heart. <3  
[12:05] TT: You know how kitchens can be. Full of deadly knives, boiling pits of oil and possible gas accidents. I needed to check on you bro.  
[12:06] TT: I know you love adventure, it's only natural I'd be worried.  
[12:06] GT: Yes yes i know! Ive seen clue i know that they can be a regular hazard for anyone that wanders into them unaware of their potential dangers.  
[12:06] TT: *treasures your heart, ironic or otherwise*  
[12:06] GT: But i assure you dirk that im FINE!  
[12:07] GT: And i reiterate! Dooork.  
[12:07] TT: I know you are. You're Jake English. Adventurer Extraoridinaire.  
[12:08] GT: Though its endearing on you. The dork thing i mean.  
[12:08] TT: Heh. So you love it. <3 I knew it.  
[12:09] TT: BTW I miss going tomb riding, you think we can schedule for next week or something?  
[12:10] TT: My swords are getting rusty.  
[12:11] GT: Hmm. Yes sure! Why not.  
[12:12] GT: My guns arent in much better shape and it has kinda been a while.  
[12:12] TT: Great. I'll start packing my stuff tonight.  
[12:13] GT: Packing?  
[12:13] GT: Er. I guess this is going to be a long excursion?  
[12:14] TT: It can be if you want. I was just referring to some weapons, munnition and foods but we could maybe go camping and stay some days away?  
[12:15] TT: Would you like that?  
[12:15] GT: Hmm. I think it sounds fun enough sure!  
[12:16] TT: *hell fucking yes* I'll start packing tonight all the more then.  
[12:17] GT: Capital!  
[12:17] GT: And sorry for the general brevity of replies dirk. Im kinda eating while chatting.  
[12:17] TT: What are you eating?  
[12:19] GT: Just a can of soup i heated up.  
[12:19] GT: I didnt have too much else so i just went with that. I probably could have gone for something with pumpkin though.  
[12:21] TT: Hm, I made myself sandwich. So it's like we're eating together now. Pass me the salt? Heh.  
[12:26] TT: *can't wait anymore* Jake? Are you ok?  
[12:28] GT: Pfft!  
[12:28] GT: Im here yes.  
[12:28] GT: Sorry i was staring at something.  
[12:29] GT: So were like having a dining date or something??  
[12:29] GT: Assuming you still want that salt.  
[12:29] TT: Yes, this is exactly that. And the salt would be nice, please.  
[12:29] GT: *Kindly passes the salt!*  
[12:29] GT: There you are my good man.  
[12:30] TT: (and what where you staring at? If something looks dangerous I'll send my bot right at it, you just have to say it once).  
[12:30] TT: Thank you, you're very kind. What a lovely evening this is.  
[12:33] GT: (No no its nothing dangerous! Sheesh dirk you dont have to hover like that. If im in serious trouble youre the first on my list.)  
[12:34] TT: (Ok. Sorry. I'll shut up.)  
[12:34] GT: Im pretty sure it could only be better if champagne and cavier were involved.  
[12:34] GT: Possibly some candlelight.  
[12:34] GT: Given this seems to be a sorta rp thing though i guess technically we could write that in???  
[12:34] GT: Is that how it works?  
[12:34] GT: Im not all that up to date on the dos and donts of rp.  
[12:35] TT: Yeah, why not. *Lights two white candles and pours some champagne into two glasses*  
[12:36] TT: Here. *hands you one*  
[12:36] TT: You look beautiful tonight. Did you do something with your hair?  
[12:37] GT: *Taps glass against Dirk's with a CHINK.*  
[12:37] TT: *CHINK CHINK yo*  
[12:37] GT: Not especially now! This is how it always looks. Though if you want i can have a bow in it maybe.  
[12:37] GT: An extremely ironic bow that takes up half my head.  
[12:40] TT: It looks great on you. I hope you don't mind the lack of caviar though. All I have is this exotic soup I made with herbs from the highest peak in the eastern mountains, took three days to gather them all. And this sandwhich here?  
[12:40] TT: Bread from the best bakers in the Old Continent, meat from the finest birds, bought to the riches princes of the East.  
[12:41] GT: Oh my golly man. Youre so friggin cheesy its bypassing dorky and shooting straight into hilarity! But i still have a fondness for it at least.  
[12:41] GT: Glad to see youre having such a wild love affair with your sandwich. And i guess im having an equally lecherous time with this soup.  
[12:42] TT: Only the best for you, my darling. *sips on his Tab-champagne*  
[12:44] GT: *Joins in on the sipping.*  
[12:45] GT: So where did you even find this tab champagne??  
[12:46] TT: That was a dark and rather gory venture I'd rather tell you about some other day. Let's not ruin the mood.  
[12:46] TT: Is your chair comfortable? I could fluff a pillow for you.  
[12:48] GT: The most comfortable! Its like sitting on a friggin cloud dirk.  
[12:48] GT: My bum is in a cushiony ass heaven at present and fluffing a pillow would only ruin shit somehow.  
[12:49] TT: Excellent. It shouldn't be any other way.  
[12:51] TT: Dining with you has been a delightful experience. We should do it again soon. Maybe I'll even get to accidentally touch your knee under the table next time. it wouldn't be a perfect night otherwise *wink*. Also I never got to mention how your dress matches your eyes.  
[12:53] GT: My dress also matches my bow. I really think the satin feel and sleeky look is accenting my natural curves too! Clearly thats a bonus for the both of us.  
[12:53] GT: I dont mind saying that i feel absolutely *stunning* dirk. This crossdressing thing was a GREAT idea. Btw im rather fond of your dress too.  
[12:56] TT: I spent all day choosing it. The burgundy velvet goes just right with my blonde mane. And the way it opens to reveal a long leg just does justice to my slender physique.  
[12:57] GT: That and it makes the accidentally knee touches that much more intimate.  
[12:57] TT: It also distracts from the hidden katana tied to the covered leg.  
[12:57] GT: What do you think dirk? Should i have gone for the double slit or is the more modest version better suited to my legs?  
[01:00] TT: I don't think I'm sure about that, since I've spent most of the evening staring at your captivating eyes. You'll have to wear both of them for me to reach a justified decision.  
[01:00] GT: Yes well my eyes ARE my best feature. Aside from my supposedly premium behind.  
[01:00] GT: Not that you can see that from your vantage point anyhow.  
[01:02] TT: Another perfect reason for you to walk the catwalk for me.  
[01:03] TT: If you wear the double slit design please leave your guns on.  
[01:03] GT: Obviously!  
[01:03] GT: One on each hip. Thats the only way to have a slit dress with pistols.  
[01:03] GT: So one and then the other?  
[01:04] \-- timaeusTestified [TT] is thinking "hell fucking YES..." --  
[01:04] TT: Yes, take your time. I'll be right here taking down notes. This is a most delicate decision.  
[01:05] GT: The most delicate! Heres hoping i get full marks on one dress or the other.  
[01:05] GT: *Gets up and locates the catwalk. Briskly but elegantly waltzes down it!*  
[01:06] TT: *takes in every little detail, like the way the fabric embraces your fit body, how it flows with your calculated movements and how much it leaves to the imagination*  
[01:06] TT: *taking down some serious notes*  
[01:09] TT: Legs: 9, Hips: 10, Back: 8, Ass: 10, Color: 9, Jake: 10  
[01:09] GT: Pfft! Theres a *jake* category?  
[01:11] TT: It's the most important category. There would be no point to this if it wasn't for the Jake factor. Do continue. This is most relevant to my interests.  
[01:12] GT: The slitted dress is going to have a lot to live up to. Those are some high marks.  
[01:12] GT: Alright though lets see if it *and* i can pull this thing off!  
[01:13] TT: *biting on his pen*  
[01:13] GT: *Heads backstage and promptly changes into another nondescript dress with two slits on the hips. Proudly wanders out and onto the catwalk and spins glamorously!*  
[01:15] TT: *chokes* *starts writing without ever losing eye-contact with each and every curve in that hot dress, and oh god, the way the guns are there adorning the whole thing...*  
[01:16] TT: Shit Jake. You outdid yourself. You should be ashamed, you'll leave all those poor Miss Universe canidadtes with no hope.  
[01:17] TT: *looks at his notes, they're all weird scribbles but he can read: Legs: 10, Hips: 10, Back: 10, Ass: Heavenly, Guns: Sexy, Jake: Fucking PERFECT.  
[01:20] TT: **IRL Dirk is already hot and bothered, slowly touching himself through his clothes to the whole image**  
[01:20] GT: Pfft! So this dress wins by a large margin.  
[01:20] GT: Or as large as it can be.  
[01:20] GT: Glad to see we got that over and done with! Whew.  
[01:21] GT: Do you want to try doing your own fashion show or...??  
[01:21] TT: So very large.  
[01:21] \-- golgothasTerror [GT] doesn't know if he should be amused or not, though he's going with yes. --  
[01:21] TT: You would like that?  
[01:24] GT: Hmm.  
[01:24] TT: Hmm?  
[01:25] TT: Is that a 'yes' hmm or a 'fucking yes' hmm?  
[01:28] GT: Lets go with a yes! But ill abstain from grading you bro.  
[01:29] GT: I wouldnt want you to feel self conscious when you scored me as high as you did.  
  
[01:29] TT: I wouldn't want you to feel uncomfortable. Just sit back and enjoy the show.   
[01:29] \-- timaeusTestified [TT] is enjoying this more than he probably should --   
[01:31] TT: *i get on the catwalk with my burgundy velvet dress first, walking slow like a panther, hips swaying so slightly, striking poses like i don't care, my leg revealed every once in a while for your viewing pleasure*   
[01:32] TT: *no cap but the shades stay on.*   
[01:35] GT: Bravo dirk! *Applauds loudly and even gives a wolf whistle every once in a while!*   
[01:35] GT: Truly a performance to be remembered bro!   
[01:36] TT: You've seen nothing yet. *goes backstage*   
[01:39] GT: Theres more?   
[01:42] TT: *when I appear I'm wearing a short, tight black leather dress, high stockings adorning my legs that end in these dangerous high heels, I walk all the way to a pole that is conveniently there, do some lazy turns around it before reaching you and doing this little sexy lap dance, long enough that you can smell my sweet perfume, but not long enough to touch, i finish with a wink showing you my hazel   
[01:42] TT: eye for a second before walking away without ever looking back*   
[01:43] GT: Oh my god dirk.   
[01:43] \-- timaeusTestified [TT] is properly touching himself now, fully exposed, waiting for the green text to pop up in his screen and God he expects Jake to be enjoying this as well. --   
[01:45] TT: You don't have to emit judgement. It's on the house.   
[01:48] GT: Dirk. I.   
[01:48] GT: Um.   
[01:49] GT: Thats.   
[01:49] GT: I didnt realize you were so into this whole rping thing. Now i feel a little bad for phoning it in.   
[01:50] TT: I ...don't do things half-heartedly.   
[01:51] TT: Was it any good?   
[01:52] GT: Um. Yes.   
[01:52] GT: I guess so. A little on the strange side but entertaining enough!   
[01:52] GT: What should we do next?   
[01:54] TT: Uhm, what would you like? I'd do anything you wanted. I'm yours for the night.   
[01:54] GT: Um... Im not sure.   
[01:54] GT: I dont quite get how these rp things typically go. I think i said that earlier.   
[01:54] GT: What do *you* want to do?   
[01:55] TT: Just talking to you is good enough. But I wouldn't want you to get bored.   
[01:55] TT: Have you finished eating?   
[01:55] \-- timaeusTestified [TT] forgot about his sandwich ages ago --   
[01:58] GT: A while ago yes!   
[01:58] GT: And really if you want to do something then im fine with it.   
[01:58] GT: Like if you want to continue playing i mean.   
[01:58] TT: Good. Yeah, ok.   
[01:59] TT: You know, I never got to touch your knee under the table. It won't be the perfect evening if this doesn't happen.   
[02:00] \-- timaeusTestified [TT] hopes Jake will play along --   
[02:00] GT: True enough.   
[02:00] GT: Ok lets do it.   
[02:01] TT: *I sit down at the table again, wearing my black dress (my usual gloves on since they match)*   
[02:01] TT: I hope you liked the show.   
[02:02] GT: It was delightful dirk. It couldnt have been better even by a model.   
[02:03] GT: *Smiles at his chum and gives two thumbs up.*   
[02:05] TT: I've been practicing all week. You were even better though. You're a natural, you're like a raw diamond, the Cinderella that needs only a dress to surpass everyone in beauty.   
[02:05] TT: *Our knees touch and oh, looks like my stocking needs some repositioning, so my hand reaches under the table and I mistake one knee for the other*   
[02:07] TT: *This un-stocking-ed knee is so much softer, I like it better than mine so I absently stroke it instead*   
[02:07] GT: *Momentarily jumps! With all this knee stroking going on, it's hard to fight the blush that crosses his cheeks!*   
[02:08] \-- timaeusTestified [TT] bites back a moan --   
[02:09] GT: Dirk. I uh. You know.   
[02:10] TT: That blush is like the icing on the cake... what is it?   
[02:12] TT: You can tell me.   
[02:16] GT: Its just um. That feels... nice.   
[02:19] TT: *the stroking slowly moves upwards along your thigh, and I lean forward, my face closer to yours* ...does it? Do you want it to continue? It could feel even better.   
[02:19] \-- timaeusTestified [TT] is taking every chance here, putting everything at stake --   
[02:20] GT: I...   
[02:20] GT: *Blushes a rather bright shade of red. Quietly puts his hand over Dirks and nods.*   
[02:21] GT: What should i do?   
[02:21] \-- timaeusTestified [TT] swallows --   
[02:22] TT: *I stand up and walk around the table to kneel by your side, grabbing your hand and kissing it* Just stay still my dear, and let me do the job. *My hands rests on your knee again, and I lean down and kiss your thigh*   
[02:23] GT: Woah!   
[02:23] GT: Dirk??   
[02:24] GT: *Jumps again, anxiously biting his lower lip and staring down at Dirk. He tilts his head to the side uncertainly.*   
[02:24] TT: Well it's out there, it's hard to resist the temptation.   
[02:24] TT: That's what these dresses do.   
[02:25] TT: *Places kisses trailing upwards towards the place where your leg disappears under the fabric*   
[02:26] TT: *briefly tugging playfully on the straps holding your weapon on the way up*   
[02:26] TT: *with his teeth*   
[02:27] GT: Oh christs burning biscuits! Dirk. I.   
[02:27] GT: Are you sure about this???   
[02:27] GT: I mean. Thats kinda. Um.   
[02:27] TT: Shhh, relax and just enjoy the ride.   
[02:27] TT: We're having healthy, free fun here. You're safe with me bro.   
[02:28] GT: Oh... yes. Haha...   
[02:28] GT: Of course!   
[02:28] GT: *Swallows hard, nodding at Dirk and the kisses.*   
[02:28] GT: *Tries not to shift excessively.*   
[02:30] TT: *one hand moves under the dress and places itself atop the neglected thigh on the other side, stroking too*   
[02:31] GT: *Shuts his eyes, his breathing slowly deepening.*   
[02:31] TT: *I look up at you and stop my movements, as if asking you for permission to go even ...*further* *   
[02:32] GT: *After a few seconds of contemplation, he smiles nervously and nods.*   
[02:33] \-- timaeusTestified [TT] has to use all of his will power not to come right there and then --   
[02:34] TT: *I tug on the dress and reveal... oh, what a nice surprise. It's lace we have here. Which I proceed to remove carefully ..using only my teeth.*   
[02:37] GT: *Tries to help Dirk remove them by slightly raising himself from his seat.*   
[02:42] TT: *I finish taking them off and go back to business, but before doing anything I stand and kiss you tenderly on the lips, since you're a gentleman and that's the proper thing to do before anything else. Before you can reply I'm on my knees again, taking your need in between my lips, running my tongue along the under side*   
[02:43] TT: *I'm probably hard too, against the hem of my short leather dress, but all I care right now is making this evening the best for you*   
[02:44] \-- timaeusTestified [TT] believes that Jake won't know how to respond, but is hopefully fantazising about everything going on, so he decides to continue typing regardless of getting replies --   
[02:45] TT: *Ignoring my own need I start working on your erection using one of my gloved hands, the other holding you in place on your heavenly soft chair*   
[02:45] GT: *Takes another deep breath, both anticipating Dirk's mouth on him and worrying that he isn't doing enough for his chum. He anxiously winds his fingertips in Dirk's hair, brushing his thumb over the strands. When Dirk's mouth is actually on him, he moans.*   
[02:45] GT: Dirk...   
[02:46] \-- timaeusTestified [TT] ohgodohgodohgod --   
[02:47] TT: *My mouth is working on you again, lips parted and tongue teasing the slit before plunging down and taking almost all of it at once*   
[02:48] GT: *He moans again, this time trying to quiet himself. These sounds are rather embarrassing, even if they're natural enough. Ever since Dirk started up his teasing, he finds himself growing harder and harder.*   
[02:49] TT: *Both my hands are now holding you in place as I bob my head up and down, pumping your length, thirsty for more, thirsty for you* Hhmmmn...   
[02:50] TT: *The straps holding your guns are the perfect handles*   
[02:51] TT: *I let it go for a moment before taking a deep breath and taking it all again, all the way to the base, swallowing around you*   
[02:51] GT: *His breath becomes less and less even, he's tempted to continue calling Dirk's name but he bits his lower lip to stop from making any noise.*   
[02:52] GT: *At least until Dirk pulls back and takes him in again. He can feel himself getting closer to the point of no return as he lets out another moan.*   
[02:52] TT: *I hum around your arousal hoping you'll continue to make those sweet sounds for me again*   
[02:54] \-- golgothasTerror [GT] starts rubbing his cheek anxiously, then shifts uncomfortably in his seat. He's feeling a reaction from all this horseplay, as embarrassing as that feels. --   
[02:56] TT: *I let go again and use my hand to stroke the lenght of your member as I go back to lapping at the tip* Hmmm... let me hear your voice again...   
[02:57] GT: *Opens his eyes, staring half-lidded at Dirk. He shakes his head while still remaining silent. After that, he sticks his tongue out at Dirk.*   
[02:59] TT: Hm. Challenge accepted. *I move lower, hand still stroking your dick while I start sucking and teasing your sack, my other hand reaching even further until one fingertip teases at your entrance*   
[02:59] TT: C'mon, sing for me.   
[03:03] GT: *Shakes his head, though he does tighten his grip on Dirk's hair.*   
[03:04] GT: *He grinds his teeth together and tries not to lean forward or thrust. He feels really close.*   
[03:06] TT: Hm, stubborn. I like that. *I go back to engulfing the whole of you in my mouth as my finger presses in, just the tip, moving around to tease the sensitive ring of muscles. My other hand grabs yours, fingers intertwined and I let you thrust up, sucking and swallowing all of you*   
[03:09] GT: *He very nearly groans when he thrusts but he manages to hold back. He does open his mouth though and breath quite heavily. He tightly holds Dirk's hand.*   
[03:13] TT: *Again I hum loudly around you, and stick my whole finger inside of you; doing my best not to choke I match the movement of my hand with your thrusts and prepare myself to swallow you whole*   
[03:14] TT: *if curling my finger and finding your prostate doesn't make you moan in delight, then I guess you'll win... this time*   
[03:17] GT: *It's the prostrate stimulation that finally gets him, and finally puts him past his breaking point. He can't hold back anymore, he calls Dirk's name midmoan and suddenly... that's it. White flashes before his eyes and he hits his orgasm. His dick twitches as he cums.*   
[03:18] \-- timaeusTestified [TT] finally lets himself go, hitting his orgasm too, hand wildly working on his erection, moaning Jake's name* --   
[03:19] \-- timaeusTestified [TT] takes a minute or so to type again after catching his breath --   
[03:21] TT: *I swallow every last drop of you, like i've been thirsty for days. When I let the softened member go I kiss it one last time before looking up at you and smiling*   
[03:21] TT: I hope you enjoyed that as much as I did. *moves his finger out of you carefully*   
[03:24] GT: *Sighs quietly, sinking bonelessly in his seat. He's still panting and feels oversensitive.*   
[03:24] GT: Yeah. That was...   
[03:24] GT: Great dirk.   
[03:24] TT: Hm see? I told you it would be fun.   
[03:26] TT: Thank you for... playing along. It was amazing. You're amazing, Jake.   
[03:26] GT: Yes it um. Yes.   
[03:27] GT: It was!   
[03:27] GT: Haha. Yeah.   
[03:27] TT: Did... did you...   
[03:27] TT: ...uh nevermind, I should start packing...   
[03:28] \-- timaeusTestified [TT] by packing he means washing his hand, it's getting hard to type with just one --   
[03:28] GT: Did i...?   
[03:28] GT: Er.   
[03:28] GT: Double nevermind. Um.   
[03:29] GT: Anyway yes! Packing.   
[03:29] GT: Packing is definitely something that should happen!   
[03:29] GT: And um. I guess if you want to do this again sometime for fun or whatever then we can.   
[03:29] TT: Yes, so much to pack, so little time.   
[03:29] GT: After all technically rp jake owes rp dirk something in return.   
[03:29] TT: And... ok, I'll take your word on it.   
[03:29] GT: He did sorta leave his chum hanging there.   
[03:29] \-- timaeusTestified [TT] "You have no idea." --   
[03:30] TT: Whenever you want.


End file.
